Caoutchouc substances and process of making same.



UNITED STATES PATENT OFFICE.

CARL HARRIES, F KIEL, GERMANY, ASSIGNOR TO EARBENFABRIKEN VORM. FRIED-R. BAYEKGa 00., OF EL BEBFELD, GERMANY, A CORPORATION OF GERMANYU CAOUTCHOUO SUBSTANCES AND PROCESS OF MAKING SAME.

1,058,056. No Drawing.

Td'aZl whom it may concern:

Be it known that I, CARL HARRIES, professor of chemistry, doctor of philosophy, citizen of the German Empire, residing at Kiel, Germany, have invented new and useful Improvements in Caoutch-ouc Substances and Processes of Making Same, 0t which the following is a specification.

I have made the surprising discovery that the alkali-forming metals, namely, the alkali and alkaline earth metals,both in an isolated "state and in the form of their mixtures, al-

dium wire prepared in the usual way arepressed into 1000 parts of butadiene (condensed, by strong'cooling) having the. formula: v

tin

The vessel is closed and allowed to stand for a week or two. The sodium is then destroyed by alcohol or water and the caoutchouc substance which has been formed is rolled into sheets. It is an elastic whitish substance soluble inbenzene. It forms a nitrosite which is a yellowish powder which becomes brown and is decomposed on being heated to 140 C. Its brom addition product is a whitish powder. Its ozonid obtained with ozone (6-7 per cent.) is a colorless oil which detonates when heated: In

the vulcanized state it is whitish and nonadhesive. g

If in the example the quantity of sodium is replaced by 100 parts of sodium amalgam containing 10 per cent. of sodium, theproduct obtained from the mixture after several days standing is identical with the caoutchouc described in the exainple.

100 parts of isoprene are mixed with 3 parts of sodium and the mixture is heated in Specification of Letters Patent, Application med November 4, 1911. serial 1m 658,536.

the butadiene series,

Patented Apr. 8, 1913.

an autoclave to 36 C. for 6 weeks. The mass is then further treated as above described.

Instead of sodium, calcium, potassium, lithium'or mixtures of these metals such as calcium-sodium and instead of sodium amalgam other amalgams such as ammonium amalgam, etc., may be used. These metals, whether used in an isolated condition alone or in the form of mixtures or alloys or amalgams, are all embraced within the generic term,alkali-forming metals. Other hydrocarbons of the butadiene series can be employed e. g. alpha-methyL, alpha-alphadin1ethyl'-, beta-gamma-dimethyl-, gammametl1yl-, beta-isobutyl-, beta-normalpropyl butadiene, etc. I The new caoutchouc substances are whitish substances soluble in benzene. They are free from protein substances which are always. contained in the natural caoutchouc and play an important part in it with regard to the elasticity of the natural caoutchouc. They form ozonids, nitrosites and brom addition products which are in the vulcanized form grayish, non-adhesive substances.

The new compounds thus obtained are different from the caoutchouc hitherto obtained from butadieneor its homologues, etc., and yield different derivatives.

The insoluble nitrosite for instance of the known isoprene caoutchouc (probably formula C H N O decomposes at about 120 C. the soluble one (formula of soluble.

product C H N O decomposes at about 162 C. while the corresponding derivatives obtained from the products of the present application (probably formula of solubleproduct C 'H N O are not even -decomposed at 220 C. The ozonids show'characteristic diflierences. The decomposition products obtained by the action of water or 1. The process of producing caoutchouc of glacial acetic acid on the ozonids presubstances which comprises subjecting hydrocarbons of the'butadiene series to the action of an alkali-forming metal.

2. The process of producing caoutchouc substances which comprises subjecting. hy-

drocarbons of the butadiene series to the action of an alkali metal.

substances which comprises subjecting hydrocarbons of the butadiene series to the action,- of sodium.

4.. The process of producing caoutchouc substances which comprises subjecting butadiene to the action of an alkaliforming metal.

5. The process of producing caoutchouc substances which comprises subjecting butadiene to the action of an alkali metal.

6. The process of producing caoutchouc substances which comprises subjecting butadiene to the action of sodium.

benzene, being free from protein substances and forming nitrosites; ozonids and brom addition products and in the vulcanized roac es form are whitish to grayish substances which are not adhesive and the ozonids of which on decomposition with water do not show the pyrrol test or show it only very weakly, substantially as described.

8. A new caoutchouc substance comprising butadiene caoutchouc obtained b treat- 3. The process of producing caoutchouc ment of butadiene with an alkali orming metal which is a whitish substance soluble in beiizene, forming a nitrosite which is a yellowish powder which becomes brown and is decomposed on being heated to 140 0.; forming a brom addition product which is a whitish powder, forming an ozonid which is a colorless oil detonating when heated and which on decomposition withwater does not show the 'pyrrol test or shows it only very weakly; and in the vulcanized form is a whitish not adhesive powder, substantially as described.

In testimony whereof I have hereunto set my hand in the presence of two subscribing witnesses.

CARL HARRIES.

Witnesses:

JULIUS Borne, Fmnnmon Burrow. 

